The Florida Keys & Key West

Calendar of Events

December 2019: Florida Keys Events

Image for Diving With a Purpose, 15 Year Odyssey: Restoring Our Oceans, Preserving Our Heritage
  • Jun 3, 2019 - Dec 31, 2019 Location: Islamorada Category: Arts & Culture
  • Diving With a Purpose, 15 Year Odyssey: Restoring Our Oceans, Preserving Our Heritage
  • Website
  • Multiple groups such as Diving With a Purpose, the Florida Keys National Marine Sanctuary, Biscayne National Park, and more have spent 15 years working together to showcase cultural and natural resources throughout the country. They focus in the protection, documentation, and interpretation of African slave trade shipwrecks and the maritime history and culture of African-Americans. This new exhibit at the History of Diving Museum, mile marker 82.9, highlights several shipwrecks and aircraft and the archaeological processes used to study them.
Image for Marathon Community Theater presents: A Greater Tuna
  • Nov 14, 2019 - Dec 7, 2019 Location: Marathon Category: Arts & Culture
  • Marathon Community Theater presents: A Greater Tuna
  • Website
  • What do Arles Struvie, Thurston Wheelis, Aunt Pearl, Petey Fisk, Didi Snavely, and Bertha Bumiller have in common? In this hilarious send-up of small-town morals and mores, they are all among the upstanding citizens of Tuna, Texas’ third-smallest town. Greater Tuna, the prequel to the Theater’s 2014-15 season’s "A Tuna Christmas,”features two actors creating the entire population of Tuna, Texas. A tour-de-farce of quick change artistry, our two actors travel across the stage like two whirling dervishes donning costume after costume, persona after persona. Two actors, twenty characters, and a barrel of laughs, y’all. Showtimes 8 p.m.; Sunday matinee 3 p.m.
Image for Key West Holiday Fest
  • Nov 27, 2019 - Dec 31, 2019 Location: Key West Category: Arts & Culture
  • Key West Holiday Fest
  • Website
  • A merry range of celebrations during Key West's busy holiday season includes the Harbor Walk of Lights, Holiday Historic Inn Tours and a lighted boat parade with festively lit vessels and good cheer. Other events include the annual hometown holiday parade, festive island lights tours via the Conch Tour Train and Old Town Trolley, seasonal artisan markets and bazaars, pet photos with Santa, a “Violins in Motion” concert and multiple New Year’s Eve “drops” that spoof New York City’s annual Times Square “ball drop.”
  • Dec 1, 2019 - Jul 31, 2020 Location: Key West Category: Fishing
  • Key West Fishing Tournament
  • Website
  • Anglers of all ages and abilities can target more than 40 species of fish in the Key West Fishing Tournament, a free-entry multi-division challenge that takes place Dec. 1 to July. 31, 2020. The tournament features divisions for men, women, junior anglers ages 10 to 15 and Pee Wees under 10 years old — making it ideal for extended families and multigenerational groups who want to share the angling experience.
Image for I Love Stock Island Holiday Lighting Ceremony
  • Dec 1, 2019 Location: The Lower Keys
  • I Love Stock Island Holiday Lighting Ceremony
  • Website
  • Join the businesses and community of Stock Island as they kickoff and celebrate the season with a festive holiday tree lighting ceremony. Free admission; held 5:30 pm - 6:30 pm. Enjoy a Welcome reception, Tree lighting, Social gathering and refreshments. Hearts are to be available for display in honor/memory of your loved ones. Located at Fishbusterz parking lot, at the corner of Maloney and 4th Street.
Image for Key West Artisan Market: Red Ribbon Day Edition
  • Dec 1, 2019 Location: Key West
  • Key West Artisan Market: Red Ribbon Day Edition
  • Website
  • Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls, from 10AM to 2PM. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Free entry & parking. Bring your own bags! We invite you to "Rock the Red Ribbon Together" and wear a ribbon or pick up a free ribbon from volunteers of the Key West Business Guild.
Image for Key West Theater presents: Max Weinberg
  • Dec 1, 2019 Location: Key West Category: Arts & Culture
  • Key West Theater presents: Max Weinberg
  • Website
  • The longtime drummer of Bruce Springsteen’s E Street Band and bandleader for Conan O’Brien’s previ-ous late-night television show, Max Weinberg, creates a truly interactive experience with “Jukebox”, inviting the audience to choose the set list, in real time, that he and his crack four-piece group will play. Doors open 7 p.m., show starts 8 p.m.
Image for World AIDS Day Service at the Key West AIDS Memorial
  • Dec 1, 2019 Location: Key West
  • World AIDS Day Service at the Key West AIDS Memorial
  • Website
  • Come out and join your friends in celebrating the lives of loved ones in Key West, the first United States City to have an AIDS Memorial. . The Key West World AIDS Day Service will be held at the AIDS Memorial, at the foot of White Street and the Edward B. Knight Pier, on Sunday, December 1 at 5 pm. The service begins with a candlelight Memorial March from the Key West City Hall down White Street to the Memorial.  Marchers will assemble at 4:30 PM.
  • Dec 4, 2019 - Dec 7, 2019 Location: Marathon Category: Arts & Culture
  • Zonta’s Festival of Trees
  • Website
  • The annual Festival of Trees is to take place at the Florida Keys Country Club. Holiday trees are festively displayed, and decorated by members of the Zonta Club of Marathon, a humanitarian service organization. Visitors and residents can view and bid to purchase the decorated trees between 5-9 p.m., and Saturday, Dec. 7 from noon to 4 p.m. Wednesday, December 4, begins at 5 pm with an all-new Children’s Night. Santa Clause will be there to visit with all the good little boys and girls and to hear what they want for Christmas this year. There will be juice and cookies and, of course, lots of decorated trees for your enjoyment.
Image for Key West Lighted Bike Ride
  • Dec 4, 2019 Location: Key West
  • Key West Lighted Bike Ride
  • Claire Hiller at 305-809-5000 Email Website
  • The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Key West for the holidays. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Entry for the bike ride is an unwrapped toy or monetary donation for Holiday Helpers. Wesley House Family Services coordinates this bike ride - registration begins October 1 online. This year the Coke Florida Caravan will be in Bayview Park to provide free photos with Santa along with cookies (from Winn Dixie) and milk - 5pm – 7:30pm. The Lighted Bike Ride will leave Bayview Park at 7pm Entry fee for the Bike Ride is one unwrapped toy for Holiday Helpers or monetary donation
Image for Tennessee Williams Theater presents: Sutton Foster
  • Dec 5, 2019 Location: Key West Category: Arts & Culture
  • Tennessee Williams Theater presents: Sutton Foster
  • Website
  • Sutton Foster is an award-winning actor, singer and dancer who has performed in 11 Broadway shows – most recently the revival of Violet – and originated roles in the Broadway productions of The Drowsy Chaperone, Little Women, Young Frankenstein, Shrek The Musical, and her Tony Award-winning performances in Anything Goes and Thoroughly Moder. Showtime 8 p.m., Tennessee Williams Theater, 5901 College Rd.
Image for COAST is Clear Music & Arts Festival
  • Dec 5, 2019 - Dec 7, 2019 Location: Key West Category: Arts & Culture
  • COAST is Clear Music & Arts Festival
  • Website
  • Coast Projects — along with Key West Art & Historical Society, Green Parrot and Blue Heaven — are to host the Third Annual COAST Is Clear Music & Arts Festival throughout Bahama Village. The festival will feature local arts events and music by a top-notch lineup of internationally acclaimed performers including Rayland Baxter, SUSTO and Tim Reynolds, to name a few.
  • Dec 6, 2019 - Dec 23, 2019 Location: Key West
  • Old Town Trolley Lights & Sights Holiday Tour
  • Website
  • The Southernmost City is all a twinkle, as the locals decorate their historic Key West homes in a splendid cascade of lights and other decorative touches to see who can outdo the other in a friendly, holiday-inspired competition. Along with the awesome sights and excellent narration highlighting fun facts about the island, you’ll also enjoy some complimentary tasty treats like cookies and hot cider. Give you and yours the gift of Key West this year! This tour has a duration of approximately 60 minutes and departs from Mallory Square. Check website for dates and times. Tickets must be purchased online.
Image for Marathon Lighted Bike Ride
  • Dec 6, 2019 Location: Marathon
  • Marathon Lighted Bike Ride
  • Claire Hiller at 305-809-5000 Email Website
  • The Lighted Bike Ride helps to gather the needed toys for the struggling, working families of Marathon for the holidays. Families and individuals with lighted and decorated bikes ride through the streets for the community to see. Begins at the Frontage Road at the Marathon Airport. Entry for the bike ride is an unwrapped toy or monetary donation for Holiday Helpers. Wesley House Family Services coordinates this bike ride - registration is available online. This year the Coke Florida Caravan will be at the Marathon Airport to provide free photos with Santa along with cookies and milk 5 p.m. – 7:30 p.m. Lighted Bike Ride will leave the Frontage Road at 7pm.
Image for Islamorada Chamber of Commerce Florida Keys Holiday Festival
  • Dec 6, 2019 Location: Islamorada Category: Arts & Culture
  • Islamorada Chamber of Commerce Florida Keys Holiday Festival
  • 305-664-4503 Website
  • The fun is set for 4-10 p.m. at the Founders Park beach area, mile marker 87. The crowd-pleasing celebration centerpiece, a 35-foot-tall holiday tree with “magical” snow blowing from its branches, is to be lighted at 6 p.m. Kids can frolic in a magical 30-ton snow mountain during the event and watch the lighting of a 35-foot-tall community tree. Parents can bid on one-of-a-kind Keys-designed ornaments during a silent auction and explore a gift bazaar. Other activities include caroling and a holiday parade.
Image for Key West City Hometown Holiday Parade
  • Dec 7, 2019 Location: Key West
  • Key West City Hometown Holiday Parade
  • 305-809-3881 Website
  • Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at 7 p.m. at Bayview Park's Truman Avenue and White Street location. Catching tossed candy and seeing Santa are highlights for kids.
Image for TRIKW Sprint & Olympic Triathlon
  • Dec 7, 2019 Location: Key West Category: Arts & Culture
  • TRIKW Sprint & Olympic Triathlon
  • Email Website
  • The Key West Triathlon expects up to 1,000 participants and some of the sport's best known triathletes; TRIKW allows you to bask in the warm weather and the waters of the Atlantic Ocean while the rest of the country is experiencing winter. Olympic and Sprint distances. Event highlights feature an Aquabike competition this year, along with a .76 km Atlantic Ocean swim from Higgs Beach, a 20km U.S. 1 cycling ride along South Roosevelt Boulevard and a 5km run along Smathers Beach.
Image for Light Up Key Largo!
  • Dec 7, 2019 Location: Key Largo
  • Light Up Key Largo!
  • 305-451-1414 Website
  • Come get into the spirit of the holidays with the lighting of the Key Largo Xmas tree and loads of fun activities for the kids. Sponsored by the Key Largo Chamber of Commerce, holiday happenings with live music, decorations, food and drinks are to spark the seasonal spirit. The annual tree lighting is to be held at the Murray E. Nelson Government Center and Key Largo Cultural Center, MM 102, from 5-9 p.m. Eggnog, caroling and an appearance from Santa and Mrs. Claus are virtually guaranteed to put everyone in a festive mood.
Image for Second Annual Lighting of the Lighthouse & Boat Parade
Image for Fifth Annual Islamorada Half Marathon and 10K
  • Dec 8, 2019 Location: Islamorada
  • Fifth Annual Islamorada Half Marathon and 10K
  • Robbie McClung 305-587-0901 Email Website
  • Winter distance runners in the Florida Keys can welcome warmer climes and the return of Islamorada's annual Half Marathon, 10k and the run-for-fun Beach N' Beer Mile. The subtropical road race is open to bucket list runners or newbies of all ages and skill levels. Registration is open for the half-marathon and 10k events Saturday, Dec. 7. At noon the fun-while-you-run Beach N' Beer Mile kicks off from the iconic Robbie's Marina, mile marker 77.5 bayside. The main half-marathon and 10k events Sunday also begin at Robbie's Marina.
Image for Tucker Degraw Memorial Christmas Boat Parade
  • Dec 8, 2019 Location: Marathon
  • Tucker Degraw Memorial Christmas Boat Parade
  • Website
  • Christmas lights on outriggers, Santa's elves and brightly lit deck displays highlight the beautiful festivities during the Key Colony Beach Boat Parade. Set to begin at dusk from the 7th Street canal, the parade is open to all boats, and the route visits canals and cuts, and passes city hall three times. Great viewing spots include Sadowski Causeway at MM 53.5 and the dock area behind city hall and the post office. The public is welcome. Sponsored by the Key Colony Beach Fishing & Boating Club
Image for Heirloom Art Auction
  • Dec 8, 2019 Location: Key West
  • Heirloom Art Auction
  • Website
  • Staged at the Hemingway Rum Company, 201 Simonton St., this evening begins at 5:30 p.m. with appetizers prepared by Iron Chefs and signature rum drinks, followed by a live art auction of pieces from the estate of Judge Tegan Slaton and his widow Rosemary Enright. Proceeds are to benefit the Wesley House. Admission is $20, and is applied toward any art purchase.
Image for Third Annual Eaton Street Christmas Stroll
  • Dec 8, 2019 Location: Key West Category: Arts & Culture
  • Third Annual Eaton Street Christmas Stroll
  • Website
  • Key West Theater, The Studios of Key West, St. Paul’s Episcopal Church, Tropic Cinema, Keys Choral Arts & Key West United Methodist Church reunite for a “new” Christmas tradition! During this new holiday tradition on Eaton Street, each venue will host a short Christmas-themed performance with caroling as you walk from presentation to presentation. The evening will begin at 4 p.m. at St. Paul’s Church. Tickets are $25 per person, available online
  • Dec 9, 2019 - Dec 22, 2019 Location: Key West
  • Conch Tour Train - Holiday Lights Tour
  • Website
  • Join the Conch Tour Train for their annual holiday lights tour of the island. To get things started we will serve up some holiday cheer with cider and cookies. Then it is all aboard for an hour tour that takes you to all of the island’s most elaborately decorated houses, buildings and neighborhoods and caroling. Departs from Key West High School, 2100 Flagler Ave., tour is approximately 60 minutes and departs from Mallory Square. Check website for dates and times.
Image for Full 'Cold' Moon Kayak Tour and Adventure with Blue Moon Kayak
  • Dec 12, 2019 Location: Key West
  • Full 'Cold' Moon Kayak Tour and Adventure with Blue Moon Kayak
  • SIGN UP 305-209-8303 Email Website
  • Paddle under the glowing sunset and the rising moon. Perfect for all ages and skill level. This trip will have you howlin’ at the moon with the cool breeze and sounds of water splashing against your kayak as you paddle. During the paddle, we break for our popular S’Mores, an American tradition consisting of graham cracker, marshmallow and Hershey chocolate sandwiched together. A delight with everyone. Guests are welcome to bring small coolers filled with favorite beverages and snacks. From 6-8 p.m., depart from Sunset Marina, 5555 College Rd. Book online or call to reserve.
Image for Waterfront Playhouse presents: Around the World in 80 Days
Image for Third Annual I Love Stock Island Festival
  • Dec 13, 2019 - Dec 15, 2019 Location: The Lower Keys Category: Arts & Culture
  • Third Annual I Love Stock Island Festival
  • Jill Snodgrass 573-680-5468 Email Website
  • Celebrate Stock Island's culture and heritage with culinary offerings featuring fresh-off-the-boat seafood, wine and beer tastings, history and art studio tours, live music and other elements that showcase the eclectic island and its working waterfront. Highlights include a lighted boat parade from Stock Island Marina Village; kid's activities & Little Mr. & Miss contest, and more.
  • Dec 13, 2019 - Dec 15, 2019 Location: Islamorada Category: Fishing
  • Islamorada Junior Sailfish Tournament
  • Tammie Gurgiolo 305-240-9337 Email Website
  • Recreation for teens in the Florida Keys can mean learning from experienced local captains and mates to tie a bimini or rig ballyhoo. One weekend each year anglers aged 16 and younger can apply such lessons in this competition. A maximum of six anglers is allowed per boat. Proceeds aid Florida Keys charities. This tournament has been held since 1964, one of the oldest sailfish events in the Keys.
Image for Stock Island Lighted Boat Parade
  • Dec 13, 2019 Location: The Lower Keys
  • Stock Island Lighted Boat Parade
  • Website
  • Kick off the holiday season and the start of the I Love Stock Island Festival at the Stock Island Marina with a procession of lighted vessels in all sizes – kayaks, dinghies, fishing boats, sailing ships, private yachts and more!  Get merry with plenty of free parking, food from Matt's Stock Island, Salty Oyster, The Barrel House, food trucks and more, along with easy viewing of the parade of watercraft. Free, family-friendly and open to the public! Starts at 7 p.m.
Image for Taste of Stock Island
  • Dec 13, 2019 Location: The Lower Keys
  • Taste of Stock Island
  • Website
  • Get off the beaten path and eat your way across Stock Island in a matter of hours as part of the annual I Love Stock Island Festival. From 4-7 p.m., taste a selection of curated plates and beverages at the locals’ favorite spots, and experience one of the Keys’ hidden gems. Plus, be some of the first to experience The Perry's new BBQ & Brews restaurant, The Barrel House! Limited tickets available, purchase online here.
Image for 12th Annual Rudolph Red Nosed 5k Run
  • Dec 14, 2019 Location: Key West
  • 12th Annual Rudolph Red Nosed 5k Run
  • Website
  • Don your festive holiday running attire, affix your ruby-red nose, and join in the fun, starting and ending at the Southernmost Beach Café,1405 Duval St. Race day check-in starts at 7 a.m. with 8 a.m. start time. After the race, enjoy refreshments, fun, prizes and a huge silent auction.
Image for Free Outdoor Pops-in-the-Park Band Concert: Suite Dreams
Image for Boot Key Harbor Christmas by the Sea Lighted Boat Parade
  • Dec 14, 2019 Location: Marathon
  • Boot Key Harbor Christmas by the Sea Lighted Boat Parade
  • Website
  • Hosted by Marathon Marina and Resort, boats of all sizes, dinghies to yachts, sail or power, are invited to show off their holiday decorating skills. Parade starts at 6 p.m. and winds through Boot Key Harbor and ends with a festive gala at Marathon Marina and Resort at 8:30 p.m. Spectators welcome! A $500 Grand Prize is up for grabs with additional prizes for best in each division.
Image for 29th Annual Schooner Wharf Bar Lighted Boat Parade
  • Dec 14, 2019 Location: Key West
  • 29th Annual Schooner Wharf Bar Lighted Boat Parade
  • 305-292-3302 Website
  • Lighted and decorated vessels from rowboats to tall ships proceed around Key West's Historic Seaport and harbor areas. Festivities are to begin at 6 p.m. with the children of Gerald Adams Elementary Steel Your Heart Band! Parade is scheduled to begin at 8 p.m. Holiday revelers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport as vessels of all shapes and sizes dazzle the crowd.
Image for Sixth Annual Parade of Paws and Shopping Bazaar
  • Dec 14, 2019 Location: Key West
  • Sixth Annual Parade of Paws and Shopping Bazaar
  • 305-294-4857 Website
  • Bring your dogs, wear a t-shirt with a picture of your kitty with pride, or walk with a paddle displaying your pet's photo! Shopping Bazaar inside the dog park features entertainment, food vendors, a Kissing Booth, holiday gifts for that special snuggle bug and more! A unique opportunity to support the lifesaving mission caring for the Keys' community's homeless animals, the event supports the Florida Keys SPCA. Check in is 9 a.m. Event is from 10 a.m. to 2 p.m., Higgs Beach, at the Higgs Dog Park. Bring four-legged friends to meet the reigning King and Queen.
Image for Christmas on the Sheriff's Animal Farm
  • Dec 15, 2019 Location: Key West
  • Christmas on the Sheriff's Animal Farm
  • 305-293-7300 Website
  • From 1-3 p.m., kids and adults can visit the furry, fluffy and feathered residents of the Animal Farm and petting zoo and get a photo taken with Santa. The Monroe County Sheriff's Office Animal Farm is situated at the county's detention center just outside Key West at 5501 College Road. This event is free and open to the public. The Sheriff's Animal Farm is open the second and fourth Sundays of the month.
Image for Rams Head Production presents: Bret Michaels at Key West Theater
  • Dec 15, 2019 Location: Key West Category: Arts & Culture
  • Rams Head Production presents: Bret Michaels at Key West Theater
  • Website
  • As front man for the legendary rock band Poison, Bret Michaels has sold 25 million records and scored an amazing 15 chartbusting Top 40 singles including "Talk Dirty To Me," "Something To Believe In," "Nothing But A Good Time" and the timeless #1 smash "Every Rose Has Its Thorn." After more than 25 years in the business this award winning, multi platinum superstar's career continues to move at warp speed. Doors open 7 p.m., show starts 8 p.m.
Image for Winter Wonderland at Crane Point Museum & Nature Center
Image for Key West Artisan Market: Holiday Shop Local edition
  • Dec 15, 2019 Location: Key West
  • Key West Artisan Market: Holiday Shop Local edition
  • Website
  • Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls, from 10AM to 2PM. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Free entry & parking. From 10 a.m. to 2 p.m., at Clarence H. Higgs Memorial Beach. Bring your own bags. A fantastic, family-friendly, free event. The show will be stocked with keys-made items perfect for gift giving this holiday season.
Image for South Florida National Parks Trust presents 'Tortugas Tales'
  • Dec 17, 2019 Location: Key West
  • South Florida National Parks Trust presents 'Tortugas Tales'
  • Website
  • Staged at the Florida Keys Eco Discovery Center, 35 E. Quay Rd., the event is to feature stories from the Dry Tortugas as presented by award-winning authors James Kushlan and Kirsten Hines and updates on Dry Tortugas National Park and its education programs by park manager Glenn Simpson and lead ranger Curtis Hall. 'Tortugas Tales' coincides with the release of a new history book on the Dry Tortugas as an opportunity to feature Dry Tortugas National Park, its human and natural history, current stewardship, visitor opportunities, and to highlight Dry Tortugas National Park educational programs supported by the South Florida National Parks Trust. Event is free and open to the public. Doors open 6 p.m., presentations begin 6:30 p.m. RSVP online.
Image for Paint Night Class: Keys Style Holiday Ornaments
  • Dec 18, 2019 Location: Marathon
  • Paint Night Class: Keys Style Holiday Ornaments
  • Website
  • Follow along for step-by-step instructions to paint a mermaid and starfish ornament, or choose from several stencils and create your own. Starts at 5:30 p.m., at Overseas Pub & Grill, registration required, cost is $35 pp, sign up online here. A $5 donation per painter benefits the Florida Keys SPCA of Marathon.
Image for Pop & Pour at The Perry: Holiday Ornament Edition
  • Dec 19, 2019 Location: The Lower Keys Category: Arts & Culture
  • Pop & Pour at The Perry: Holiday Ornament Edition
  • Website
  • Join artist Jasmine Jones of Ocean Blues Studio for The Perry's version of a 'paint & sip’ class! In true island style, attendees will be painting under the palm trees, but with a holiday twist. This class starts at 7 p.m. at the Salty Oyster, will feature ornament painting, perfect for decorating your own home or for gift-giving. Great for all-ages, and 21+ get a complimentary drink ticket with class purchase! Class $50, includes three ornaments. Limited seats, reserve spot online.
Image for Tennessee Williams Theater presents: The Play That Goes Wrong
Image for Discovery Saturday Educational Series: Coral Crafts
  • Dec 21, 2019 Location: Key West
  • Discovery Saturday Educational Series: Coral Crafts
  • Website
  • Kids in kindergarten through fifth grade are invited to join the free, fun-filled Discovery Saturday at the Florida Keys Eco-Discovery Center (35 East Quay Road, Key West) from 10-11 a.m. Hosted by Reef Relief, children will make candy coral crafts and learn. Free admission, free parking. Discovery Saturday is held the third Saturday of every month. Pre-registration is recommended. The Florida Keys Eco-Discovery Center is located at 35 East Quay Road on the Truman Annex waterfront in Key West.
Image for Key Largo Boat Parade
  • Dec 21, 2019 Location: Key Largo
  • Key Largo Boat Parade
  • Marlen Weeks 305-394-1680 Website
  • Blackwater Sound will shimmer as decorated boats parade along the shoreline in celebration of the holiday season.  The best viewing and libations are to be found at Jimmy Johnson’s Big Chill, Sundowner’s Restaurant and the Caribbean Club, MM 103-104 Bayside.  The parade is free to enter; one grand prize winner and one randomly selected lucky boat are to receive $500 each.  Hosted by The Rotary Club of Key Largo Sunset, the parade starts at 7:30 p.m.
Image for Candy Canes and Kayaks
  • Dec 22, 2019 Location: Key West
  • Candy Canes and Kayaks
  • Website
  • From 5:30 - 7:30 p.m., Blue Moon Kayak Key West will take you on the Gulf and around Stock Island to view the twinkling holiday lights across the water. Join a family-friendly event with candy canes for everyone! $50 per person. Departs from Sunset Marina, 5555 College Rd.
  • Dec 22, 2019 - Dec 28, 2019 Location: Key West
  • Truman Little White House - Little White House Holiday Tours
  • Website
  • Imagine how it must’ve been to celebrate the holidays with the Truman’s in the 1940s. An impeccably appointed tree decked with the finest ceramic and glass ornaments. The intoxicating aroma of cinnamon and spruce. Now you can travel back to a simpler time with this exclusive tour with some very special treats in store! Enjoy this special tour complete with hot chocolate and treats, holiday crafts and much more. Dates: Dec. 22, 23, 27 & 28; from 6:30 - 8:30 p.m., Little White House is located at 111 Front St.
Image for Fringe Theater presents: An Evening Lost with Lillian Baxter
  • Dec 26, 2019 - Dec 31, 2019 Location: Key West Category: Arts & Culture
  • Fringe Theater presents: An Evening Lost with Lillian Baxter
  • 305-731-0581 Email Website
  • 1970s TV icon Lillian Baxter just had her show cancelled. What’s a "everything's coming up roses" girl to do? Industrial musicals, game shows, sitcoms, and Broadway for a start! Lillian reminds us that what is lost can always be found. Performance 7 p.m. at Little Room Jazz Club, 821 Duval St. Fringe Theater is Key West's community-focused theater providing unique opportunities for people to see and do theater. 
Image for 60th Annual Key West Home Tours
  • Dec 27, 2019 - Dec 28, 2019 Location: Key West
  • 60th Annual Key West Home Tours
  • 305-294-9501 Website
  • Presented by the Old Island Restoration Foundation, the annual self-guided tours from 3-6 p.m. each day showcase festively dressed Key West homes and gardens. Tickets are $35 in advance, $40 day-of-tour. You will be enchanted by exquisite restorations, creative renovations and delightful interiors featuring art collections, antiques, and much more. All proceeds from the tours stay in the Key West local community fulfilling OIRF’s mission of “Celebrating and sustaining Key West’s unique architecture, culture and history.” 
Image for Rams Head Productions presents: Blackberry Smoke
  • Dec 28, 2019 Location: Key West Category: Arts & Culture
  • Rams Head Productions presents: Blackberry Smoke
  • Website
  • Scorched-blues and Southern rock fans are going to love this show! Performances also from Georgia Satellites and Bishop Gun, of Natchez, Mississippi, rooted in the history and sounds of their home and the surrounding Delta, featuring a blend of rock and roll, soul and blues. Starts at 4 p.m. Key West Amphitheater, Truman Waterfront at 21 Quay Rd. Tickets available online.
Image for Key West Artisan Market: Bring in the New! edition
  • Dec 29, 2019 Location: Key West
  • Key West Artisan Market: Bring in the New! edition
  • Website
  • Enjoy a full bar, coffee, smoothies, natural juices and cut fruit, multiple food trucks and stalls from 10AM to 2PM. Shop a curated outdoor market offering fine crafts, art and jewelry from talented Florida Keys makers. Stock your pantry and fridge with fresh produce, artisan cheeses, local seafood, honey, pickles and so much more. Free entry & parking. From 10 a.m. to 2 p.m., at Clarence H. Higgs Memorial Beach. Bring your own bags. A fantastic, family-friendly, free event. The artists will be stocked with keys-made items perfect to treat yourself to the gift you always wanted! Plus check out the selection of wine by the bottle, great snacks for your New Year's Eve festivities and fabulous cuisine worthy of a special dinner celebrating 2020.
Image for Isla Bella Beach Resort's New Year's Eve Dinner, Dancing & Celebration
  • Dec 31, 2019 Location: Marathon
  • Isla Bella Beach Resort's New Year's Eve Dinner, Dancing & Celebration
  • Website
  • Ring in the New Year at Marathon’s new Isla Bella Beach Resort for a night of food, spectacular views and dancing the night away.  Evening includes a one-hour cocktail reception overlooking the water, dinner buffet featuring a seafood bar, carving station, creative sides, and dessert bar, followed by dancing the night away. Open to the public, reservations required. Per person fees apply.
Image for Sun Salutations and Health & Fitness Fair
  • Dec 31, 2019 Location: The Lower Keys
  • Sun Salutations and Health & Fitness Fair
  • Website
  • Enjoy the new event lawn at The Perry Hotel for '108 Sun Salutations' from 8 a.m. to 12 p.m. to end 2019 on a fit note! This donation-based event is open to the public with donations to benefit the Florida Keys SPCA animal rescue shelter. Celebrate your practice with a mimosa toast, then shop health & fitness booths including FYT Key West, Amber Air Essentials, and more. Booths open at 9:30 following yoga - please BYOM (bring your own mat).
Image for Old Island Restoration Foundation presents: 1860s or 1960s Costume Gala
  • Dec 31, 2019 Location: Key West
  • Old Island Restoration Foundation presents: 1860s or 1960s Costume Gala
  • Website
  • Travel back to the 1960’s for our 60th year anniversary themed NYE party. The fabulously dressed 21-plus crowd sets the scene. This is an exclusive event at the Garden at the Oldest House Museum, 322 Duval St. Limited Seating. The porch will also be open to watch the revelers promenade on Duval Street. Gate opens 6:00 pm; Dinner 8:15pm; Countdown at midnight. Tickets $225pp, available online.
Image for Key West Dachshund Walk
  • Dec 31, 2019 Location: Key West
  • Key West Dachshund Walk
  • Website
  • Frost-free Key West becomes a "wiener wonderland" when about 200 dachshunds and their owners take a noontime New Year's Eve stroll through the island's picturesque downtown. Spectators can watch the fun and meet the canine participants on Fleming Street between Whitehead and Duval streets.
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